Amphiphilic Cyclodextrins: Synthesis and Characterization

Perret, Florent; Parrot‐Lopez, Hélène

doi:10.1002/9780470926819.ch11

Cited by 5 publications

(8 citation statements)

References 164 publications

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“…Inclusion complexes with supramolecular structures formed by native or modified cyclodextrins (CDs) are attracting an increasing attention [ 1 – 8 ], including also the new polymeric CD nanogels [ 9 ] and nanosponges [ 10 – 13 ]. Over the past twenty years, amphiphilic cyclodextrins (aCD) formed with α-, β-, or γ-CD have given rise to a wide interest in the scientific community because of their versatility both as drug carriers [ 11 , 14 – 15 ] and as self-assembling systems for molecular recognition [ 16 – 18 ]. Different research groups investigated the aCD behaviour in solution, elucidating their nanostructures and physicochemical behaviour, including the temperature- and concentration-dependence of the supramolecular structures, or the pH dependence of water solubility, so as to improve our understanding of their activity as drug delivery systems [ 19 – 20 ] and of the biological fate of the assemblies [ 21 – 22 ].…”

Section: Introductionmentioning

confidence: 99%

“…Potential applications of non-ionic aCD as anticancer and antiviral drug nanocarriers were recently reported [ 14 ], while analogue cationic aCD with terminal short amino-PEG at the secondary rim form nanoassemblies which entrap photosensitizers for photoactivated therapy [ 25 ] or DNA for gene delivery [ 26 – 30 ]. The potential of aCD is strengthened by their ability to selectively recognize cells by exposing receptor-targeting groups on the surface of the nanoassembly [ 30 ].…”

Section: Introductionmentioning

confidence: 99%

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Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

Raffaini¹,

Mazzaglia²

2015

Beilstein J. Org. Chem.

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SummaryAmphiphilically modified cyclodextrins may form various supramolecular aggregates. Here we report a theoretical study of the aggregation of a few amphiphilic cyclodextrins carrying hydrophobic thioalkyl groups and hydrophilic ethylene glycol moieties at opposite rims, focusing on the initial nucleation stage in an apolar solvent and in water. The study is based on atomistic molecular dynamics methods with a “bottom up” approach that can provide important information about the initial aggregates of few molecules. The focus is on the interaction pattern of amphiphilic cyclodextrin (aCD), which may interact by mutual inclusion of the substituent groups in the hydrophobic cavity of neighbouring molecules or by dispersion interactions at their lateral surface. We suggest that these aggregates can also form the nucleation stage of larger systems as well as the building blocks of micelles, vesicle, membranes, or generally nanoparticles thus opening new perspectives in the design of aggregates correlating their structures with the pharmaceutical properties.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

Raffaini¹,

Mazzaglia²

2015

Beilstein J. Org. Chem.

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“…Amphiphilic cyclodextrins (aCD) are a class of molecules highly investigated for their self-assembly properties and inherent potential applications [ 1 – 2 ]. In particular, the modification with thioalkyl chains in the primary rim and oligoethylene glycol chains in the secondary rim and, consequently, their hydrophobic–hydrophilic balance ( Scheme 1 ) modulates the formation of differently sized and shaped nanoconstructs as membrane models for molecular recognition [ 3 ] or nanocarriers for drug delivery [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

Aggregation behavior of amphiphilic cyclodextrins in a nonpolar solvent: evidence of large-scale structures by atomistic molecular dynamics simulations and solution studies

Raffaini

Mazzaglia

2016

Beilstein J. Org. Chem.

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SummaryChemically modified cyclodextrins carrying both hydrophobic and hydrophilic substituents may form supramolecular aggregates or nanostructures of great interest. These systems have been usually investigated and characterized in water for their potential use as nanocarriers for drug delivery, but they can also aggregate in apolar solvents, as shown in the present paper through atomistic molecular dynamics simulations and dynamic light scattering measurements. The simulations, carried out with a large number of molecules in vacuo adopting an unbiased bottom-up approach, suggest the formation of bidimensional structures with characteristic length scales of the order of 10 nm, although some of these sizes are possibly affected by the assumed periodicity of the simulation cell, in particular at longer lengths. In any case, these nanostructures are stable at least from the kinetic viewpoint for relatively long times thanks to the large number of intermolecular interactions of dipolar and dispersive nature. The dynamic light scattering experiments indicate the presence of aggregates with a hydrodynamic radius of the order of 80 nm and a relatively modest polydispersity, even though smaller nanometer-sized aggregates cannot be fully ruled out. Taken together, these simulation and experimental results indicate that amphiphilically modified cyclodextrins do also form large-scale nanoaggregates even in apolar solvents.

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“…Amphiphilic CDs represent a new generation of modified CDs; interestingly, they are capable of forming micellar aggregates or vesicles [6,7,8,9]. By hydrophobic modification, the possibility of intimate contact of CDs with biological membranes can also be improved [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Retinol Stabilization of Fatty Amide-β-cyclodextrin Conjugates

et al. 2016

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Amphiphilic cyclodextrin (CD) has been the object of growing scientific attention because of its two recognition sites, the cavity and the apolar heart, formed by self-assembly. In the present study, mono[6-deoxy-6-(octadecanamido)]-β-CD and mono[6-deoxy-6-(octadecenamido)]-β-CD were successfully synthesized by reacting mono-6-amino-6-deoxy-β-CD with N-hydroxysuccinimide esters of corresponding fatty acids in DMF. The structures were analyzed using nuclear magnetic resonance spectroscopy and mass spectrometry. The amphiphilic β-CDs were able to form self-assembled nano-vesicles in water, and the supramolecular architectures were characterized using fluorescence spectroscopy, dynamic light scattering, and transmission electron microscopy. Using the cavity-type nano-vesicles, all-trans-retinol was efficiently encapsulated; it was then stabilized against the photo-degradation. Therefore, the present fatty amide-β-CD conjugate will be a potential molecule for carrier systems in cosmetic and pharmaceutical applications.

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Amphiphilic Cyclodextrins: Synthesis and Characterization

Cited by 5 publications

References 164 publications

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

Aggregation behavior of amphiphilic cyclodextrins in a nonpolar solvent: evidence of large-scale structures by atomistic molecular dynamics simulations and solution studies

Synthesis, Characterization, and Retinol Stabilization of Fatty Amide-β-cyclodextrin Conjugates

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